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Volumn 44, Issue 17, 1988, Pages 5525-5540

The asymmetric synthesis of α-amino and α-hydrazino acid derivatives via the stereoselective amination of chiral enolates with azodicarboxylate esters

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EID: 0000744779     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)86058-0     Document Type: Article
Times cited : (198)

References (54)
  • 3
    • 0000564744 scopus 로고
    • For a review of the use of azodicarboxylate esters in conjunction with phosophines, for the activation of alcohols in substitution reactions see: Mitsunobu, O. Synthesis 1981,1-28. For a recent mechanistic study of this process see
    • (1987) J. Org. Chem. , vol.52 , pp. 4235-4238
    • Varasi1    Walker2    Maddox3
  • 4
    • 0015901512 scopus 로고
    • For the application of azodicarboxylate esters to the dealkylation of tertiary amines see, and references therein.
    • (1973) J. Org. Chem. , vol.38 , pp. 1652-1657
    • Smissman1    Makriyannis2
  • 14
    • 0000170983 scopus 로고
    • Since the completion of this work the reaction of DBAD with aryllithium and Grignard reagents was employed in a general route to arylhydrazines
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4933-4934
    • Demers1    Klaubert2
  • 18
    • 0000261040 scopus 로고
    • Enantioselective Syntheses of ?-Amino Acids from 10-(Aminosulfonyl)-2-bornyl Esters and Di(tert-butyl) Azodicarboxylate. Preliminary Communication
    • For related studies completed concurrent to this work. see.
    • (1986) Helvetica Chimica Acta , vol.69 , pp. 1923-1926
    • Oppolzer1    Moretti2
  • 25
    • 84918150397 scopus 로고    scopus 로고
    • Fluka Chemical Corp. Cat. no. 11625.
  • 28
    • 84918150396 scopus 로고    scopus 로고
    • Hydrazide 4f (R = t-butyl) was only epimerized to the extent of 6% after heating at reflux for 9 h under the previously described conditions.
  • 29
    • 0001594845 scopus 로고
    • Asymmetric oxygenation of chiral imide enolates. A general approach to the synthesis of enantiomerically pure .alpha.-hydroxy carboxylic acid synthons
    • For the asymmetric electrophilic hydroxylation of the sodium enolate of an analogous substrate see
    • (1985) Journal of the American Chemical Society , vol.707 , pp. 4346-4348
    • Evans1    Morrissey2    Dorow3
  • 40
    • 0003905731 scopus 로고
    • For a discussion of this and related transition state hypotheses for the aldol reaction see, J.D. Morrison, Academic, New York, Chapter 2.
    • (1984) Asymmetric Synthesis , vol.3
    • Heathcock1
  • 42
    • 0000931413 scopus 로고
    • For the use of related oxazolidine derivatives as chiral resolving reagents see
    • (1983) J. Org. Chem. , vol.48 , pp. 2520-2527
    • Pirkle1    Simmons2
  • 46
    • 0002629054 scopus 로고
    • The greater reactivity of Raney nickel as compared to other catalysts in effecting N-N bond hydrogenolysis was established in preliminary studies from this laboratory (Ref. 53) and has ample literature precedent. For leading references, see
    • (1960) J. Org. Chem. , vol.25 , pp. 44-46
    • Carmi1    Pollak2    Yellin3
  • 47
    • 20444470915 scopus 로고
    • REDUCTIVE CLEAVAGE OF NITROGEN–NITROGEN BONDS WITH RANEY NICKEL AND HYDRAZINE
    • The greater reactivity of Raney nickel as compared to other catalysts in effecting N-N bond hydrogenolysis was established in preliminary studies from this laboratory (Ref. 53), and has ample literature precedent. For leading references, see
    • (1961) Canadian Journal of Chemistry , vol.39 , pp. 1171-1173
    • Robinson1    Brown2
  • 48
    • 0012073867 scopus 로고
    • The greater reactivity of Raney nickel as compared to other catalysts in effecting N-N bond hydrogenolysis was established in preliminary studies from this laboratory (Ref. 53), and has ample literature precedent. For leading references, see
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 2527-2532
    • Biel1    Hoya2    Leiser3
  • 50
    • 84918150395 scopus 로고    scopus 로고
    • The slightly lower diastereomeric purity in the phenyl glycine derivative 10d (Entry B Table 3) is assumed to reflect the enantiomeric purity of the hydrazido ester precursor 9d.
  • 54
    • 84918150394 scopus 로고    scopus 로고
    • 2 (3 × 2 mL).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.